Boards, Succession and the Path to Exit with Jonathan Bennett

In this episode, strategist and author Jonathan Bennett—advisor to CEOs, boards, and founders—breaks down exactly how and when to stand up an advisory board, why founders should hire a chair first, and how structure and accountability pull leaders out of isolation. The conversation covers paid vs. unpaid advisors, what to do when disagreements arise, and how quarterly decks become an early-warning system for both risk and opportunity.

You will hear a live case study on a $5M trades business planning a future exit, learn the baseline systems and KPIs required before a board can help, and understand how a skilled chair’s network can fill functional gaps, recruit leaders, and prep a company for sale. Jonathan also opens the curtain on his “portfolio life,” the realities of CEO coaching, and a behind-the-scenes advisory series where listeners can eavesdrop on real-world boardroom conversations.

Don’t miss this conversation between Ken Eslick and Jonathan Bennett!

Looking for your next leader? Contact us: ken@theleaderslab.co or take the Free ScaleUp Leadership Survey at theleaderslab.co

⏱️ Segments 

00:00 – Welcome & Why Boards Belong in Your Playbook (guest intro + pillars: Hire, Scale, Sell)
01:02 – Jonathan’s First Board Seat: governance by immersion and what stuck
03:12 – Feeling Alone as a Founder? Build “Scaffolding”: mentors vs. coaches vs. advisory boards
05:04 – Making It Real: 4 handpicked advisors, quarterly packs, brutal questions, accountability
07:28 – How to Get on (and Build) Boards: why young leaders should join one
10:01 – When to Form an Advisory Board—and What to Pay: from bootstrap to $20M+ examples
12:10 – The Better Model: Hire the Chair First and let the chair recruit for blind spots
14:15 – Recruiting Your Board Like a Pro: use a formal search (yes, a recruiter) and interviews
16:22 – Cadence & Consequences: quarterly rhythm, ad-hoc in crises, and what if you ignore advice?
18:45 – Virtual vs. In-Person: Zoom practicality vs. the magic of dinner + a full-day board
21:02 – Case Study: $5M HVAC/Plumbing Owner Eyeing an Exit—the chair’s profile and board mix
24:55 – Before the Board Helps, Fix the Foundation: KPIs, finance hygiene, and leveraging the board’s network
28:42 – Inside Jonathan’s Portfolio Week: four boards, executive advising, and selective consulting
30:58 – Coaching vs. Advising: decision-making, tough HR calls, and “sometimes just give the answer”
33:10 – Deep Listening & ‘Clearly Then’: why presence matters and where to hear real sessions

 

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